ES2647610T3 - Oleic Stearidonic Acid Compositions - Google Patents

Abstract

An oleic composition comprising an interesterified structured lipid component and one or more components selected from a phytosterol ester and an additional edible oil; wherein the interesterified structured lipid component is a reaction product of an interesterification reactive charge, the reactive charge (i) comprising an amount of a medium chain triglyceride having fatty acid chains from C6 to C12 in length, (ii ) an amount of a long chain household oil having fatty acid chains of C16 in length, and (iii) an amount of a stearidonic acid source, wherein the stearidonic acid source is Echium oil and the amount of Echium oil in the interesterification charge is 20-40 percent by weight based on the total weight of the reactive charge.

Description

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DESCRIPTION

Oleic Stearidonic Acid Compositions

Field of the Invention

This text provides oleic compositions comprising stearidonic acid. In some embodiments, the compositions provided herein are structured lipids comprising stearidonic acid in which stearidonic acid has improved stability. Uses of the compositions and methods for preparing such oleic compositions are also provided.

Background

Stearidonic acid (SDA), 18: 4n-3) is a highly unsaturated omega 3 fatty acid. SDA is very important in human nutrition because it is an intermediate in the biosynthesis of omega 3 fatty acids, eicosapentaenoic acids (EPA) and docosahexaenoic acid (DHA). These two omega 3 fatty acids are necessary in diets in humans for cell membrane functioning and good health (Coupland and Hebard, Stearidonic acid containing plant-seed oils: Their potential for use in healthy foods, 93rd AOCS Annual meeting and Expo, May 5-8, 2002, Montreal, Quebec, Canada.). An increased intake of omega 3 fatty acids has been positively associated with the prevention of cardiovascular diseases, arthritis, inflammatory diseases, and autoimmune diseases in humans (Simopoulos AP, 1999, Essential fatty acids in health and chronic disease, Am. J. Clin Nutr. 70: 560-569.).

Stearidonic acid is found in other species Echium (E. vulgare L.), hemp seed (Cannabis sativa L., Cannabaceae) (2% -3%) (Callaway et al. 1996, Occurence of “omega-3” stearidonic acid (cis-6,9,12,15octadecatetraenoic acid) in hemp (Cannabis sativa L.), J. Iltemp Assoc. 3 (2): 61-63.), and currant seed (Ribes nigrum L., Grossulariaceae) (approximately 2%) (Clough 1993, Sources and production of specialty oils containing GLA and stearidonic acid, Lipid Technol., 5 (3): 9-12)).

Due to the health benefits of DSA, numerous researchers have tried to prepare products that incorporate SDA. There is a continuing need for stable oleic products with SDA.

Summary

In one aspect, the present invention provides an oleic composition comprising an intersterified structured lipid component and one or more components selected from a phytosterol ester and an additional edible oil; wherein the structured lipid component is a reaction product of an reactive loading of interesterification, the reactive charge comprising (i) an amount of a medium chain triglyceride having chains of C6 to C12 fatty acids in length, (ii) a amount of a long chain household oil having fatty acid chains of at least C16 in length, and (iii) an amount of a source of stearidonic acid, where the source of stearidonic acid is Echium oil and the amount of oil of Echium in the intersterification load is 20-40 percent by weight of the total reactive load weight.

In some embodiments, the amount of Echium oil in the intersterification charge is 30 percent by weight.

In some embodiments, the medium chain triglyceride is selected from the group consisting of caprylic triglyceride, capric triglyceride, and combinations thereof. In another embodiment, the amount of a medium chain triglyceride is 30 to 40 percent by weight of the intersterification charge.

In some embodiments, the domestic long chain oil is selected from the group consisting of soybean oil, corn oil, cottonseed oil, rapeseed oil, olive oil, peanut oil, safflower oil, sunflower oil, Cereal plant oil, and their combinations. In another embodiment, the amount of domestic oil is 30 to 40 percent by weight of the intersterification charge.

In some embodiments, the amount of medium chain triglyceride is 35 percent by weight and the amount of domestic oil is 35 percent by weight of the intersterification charge.

In another aspect, the present invention provides a method for preparing an intersterified structured lipid, comprising: providing a reactive filler comprising an amount of medium chain triglycerides having carbon chain lengths between C6 to C12, an amount of oil domestic having carbon chain lengths between C16 to C22, and an amount of a source of stearidonic acid; and intersterify the reactive charge to form an intersterified structured lipid, where the source of stearidonic acid is Echium oil and the amount of Echium oil in the intersterification charge is 20-40 percent by weight based on the total weight of the charge. reactive

In some embodiments, interesterification is catalyzed by a chemical catalyst. In another embodiment, the catalyst comprises sodium methoxide.

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In some embodiments, the method further comprises a deodorization step. In another embodiment, deodorization is carried out at 214 ° C at 226 ° C.

Structured lipids comprising SDA are provided in this text. In some embodiments, oleic compositions comprising structured lipids are provided herein. In some embodiments, the oleic compositions are used instead of, or in combination with, conventional edible oleic products such as household oils.

The structured lipid provided in this text is an interesterification product of an edible domestic oil, a medium chain triglyceride, and a source of SDA.

In some embodiments, the structured lipids provided herein are combined with phytosterol esters.

The structured lipid provided herein is a reaction product of an intersterification reactive charge, where the reactive charge comprises an amount of a medium chain triglyceride having fatty acid chains of 6 to 12 carbon atoms in length, an amount of a domestic long-chain oil having fatty acid chains of 16 carbon atoms in length, and an amount of a source of SDA.

The oleic compositions provided in this text optionally comprise a phytosterol ester component, and one or more other edible oils.

The structured lipid compositions provided herein are useful in various food systems, especially baked, sauteed, sauteed in wok and as an oleic component of a dressing, marinade or other product that is used and / or stored at room temperature or refrigerated temperatures

This procedure provides a procedure to incorporate SDA into a structured lipid.

The method comprises random interesterification of a medium chain triglyceride, a source of SDA and a long chain edible oil.

The source of SDA comprises Echium oil.

The source of SDA is Echium oil.

In some embodiments, the oleic compositions provided herein also comprise a phytosterol.

Detailed description

Compositions comprising SDA are provided in this text. Additionally methods for preparing the compositions and uses of the compositions are provided. The methods and compositions are described in detail in the sections below.

US 2009/023808, US 2006/111254, EP 1714564, US 2007/218183, US 2005/266051 and WO 2008/026909 describe compositions comprising SDA.

Definitions

Unless otherwise described, all technical and scientific terms used in this text have the same meaning as usually understood by one skilled in the art. In the case where there is a variety of definitions for a term in this text, those in this section prevail unless otherwise specified.

As used herein, interesterification is a known reaction of triacylglycerol structures in which the individual fatty acid structures in the triglyceride positions that are intersterified are exchanged in the rest of glycerol.

As used herein, random interesterification is an interesterification in which the individual fatty acid structures are randomly exchanged in the rest of glycerol.

As used herein, structured lipids are triacylglycerols that have been modified to change the composition of the fatty acid and / or its positional distribution on the glycerol skeleton by chemical and / or enzymatically catalyzed reactions and / or genetic engineering. In one embodiment, the structured lipids are modified triacylglycerols with improved nutritional or functional properties.

As used herein, a reaction charge refers to reactants in the intersterification reaction provided in this text, which includes a medium chain triglyceride (MCT) having

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C6 to C12 long fatty acid chains, a domestic long chain oil that has at least C16 long fatty acid chains, and a source of SDA.

Compositions

Compositions comprising structured lipids prepared by chemical interesterification of a medium chain triglyceride, a domestic oil, and a source of SDA are provided herein.

The source of SDA in the structured lipids provided in this text is Echium oil. In some embodiments, the amount of Echium oil used in the interesterification reaction is approximately 2040% based on the total weight of the reactants. In some embodiments, the amount of Echium oil used in the interesterification reaction is approximately 20%, 25%, 30%, 35% or 40% based on the total weight of the reactants. In one embodiment, the amount of Echium oil used in the interesterification reaction is approximately 30% based on the total weight of the reactants.

The use of MCTs in the diet of humans has been well documented in the literature. For example, see, Traul et al., "Review Of The Toxicologic Properties Of Medium-Chain Triglyceride", Food and Chemical Toxicology, 38, pages 79-98 (2000) and Ingale et al., "Dietary Energy Value of Medium- Chain Triglycerides ”, Journal of Food Science, Volume 64, No. 6, pages 960-963 (1999). According to Traul et al., The safety of MCTs in the consumption in the diet of human beings has been indicated up to levels of 1 gram per kilogram of body weight.

In some embodiments, the medium chain or "MCT" triglycerides used in the intersterification process are produced commercially by fractionation and distillation of fatty acids from coconut or palm kernel oils. In some embodiments, the production of medium chain triglycerides includes esterification with glycerin to form a triglyceride having chain lengths of the C6 to C12 fatty acids. Edible oils, for example, coconut or palm kernel oils typically contain about 4 to 8 percent by weight of C8 caprylic fatty acids and between about 3 and about 7 percent by weight of C10 capric acids. Lower levels, typically between about 1 and about 2 percent by weight, of each or both C6 caproic fatty acids and C12 lauric fatty acids may be present in such products.

Exemplary medium chain triglyceride products include some NEOBEE® products such as NEOBEE® M-5 (brand and product of Stepan Company), Aldo MCT (brand and product of Lonza Inc.), CAPTEX® 300 (brand and product of Abitec Corp .), and MIGLYOLO 812 (brand and product of Clionova, Inc.)

In some embodiments, the amount of MCT used in the interesterification reaction is approximately 2545% based on the total weight of the reactants. In some embodiments, the amount of MCT used in the interesterification reaction is approximately 25%, 30%, 35%, 40% or 45% based on the total weight of the reactants. In one embodiment, the amount of MCT used in the interesterification reaction is approximately 35% based on the total weight of the reactants.

The structured lipids provided in this text further comprise domestic oils. Domestic oils for use in this text include soybean oil, corn oil, cottonseed oil, rapeseed oil, safflower oil, sunflower oil, peanut oil, olive oil, cereal plant oil , and preserved identity oils such as preserved identity rapeseed oil and the like. The edible oil for use in this text is a liquid oil. In some embodiments, the oil is used without hydrogenation. The household oils used in this text are also known as long chain lipids. In some embodiments, the chain lengths of domestic oils are between C16 and C22.

In some embodiments, household oils for use in this text are substantially unsaturated oils. In one embodiment, household oils comprise soybean oil, corn, cottonseed or rapeseed. In some embodiments, household oils are especially oils that include preserved and refined identity rapeseed oils, bleached and highly stable deodorized oils. Such a suitable oil is a low-linoleic acid soybean oil sold under the Nutrium® brand, available from the Bunge DuPont Biotech Alliance, St Louis, Missouri. Other examples are described in Sornyk et al., US Pat. No. 5,965,755 and Lanuza et al., U.S. Pat. No. 6,169,190.

In some embodiments, the amount of household oil used in the interesterification reaction is approximately 25-45% based on the total weight of the reactants. In some embodiments, the amount of household oil used in the interesterification reaction is approximately 25%, 30%, 35%, 40%, or 45% based on the total weight of the reactants. In one embodiment, the amount of domestic oil used in the interesterification reaction is approximately 35% based on the total weight of the reactants.

In some embodiments, structured lipids comprising SDA provided herein are stable for approximately 1, 2, 3, 4, 5, 6 weeks or more. In some embodiments, structured lipids comprising SDA provided herein are stable for approximately 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 15, 20, 24, 28, 30, 36, 40, 48 months or more. The stability of structured lipids can be measured

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using methods known to those skilled in the art. In some embodiments, stability is measured by analytical analyzes of free fatty acids, anisidine value, peroxide value, oxidative stability, color, and DMARD for structured lipids provided herein. In some embodiments, the structured lipids provided herein are more stable than Echium oil and / or a physical mixture of highly oleic rapeseed oil, MCT, and Echium oil.

Preparation Methods

This procedure provides a procedure to prepare structured lipids. The procedure provided in this text involves loading the reactants that include a source of SDA, a medium chain triglyceride, and a domestic oil, into a reactor vessel for intersterification. In some embodiments, such containers have means for heating the reactants during stirring and under reduced pressure or vacuum conditions. In one embodiment, the reaction is carried out in the presence of a suitable interesterification catalyst and typically proceeds rapidly to substantially complete or complete. In some embodiments, interesterification is a reaction to or towards complete randomization, which should mean a degree of interesterification of 100% of the acyl fatty chains.

In some embodiments, the interesterification catalysts include metal alkoxides, alkali metals, alkali metal alloys, and metal hydroxides. In some embodiments, the alkoxides include alkali metal alkoxides, such as sodium methoxide, sodium ethoxide, potassium methoxide and potassium ethoxide. In some embodiments, alkali metals include sodium. In some embodiments, alkali metal alloys include sodium / potassium alloy. In some embodiments, metal hydroxides include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide. In one embodiment, the catalyst is sodium methoxide. In some embodiments, the catalyst is present in less than 1% by weight of the intersterification mixture, in some embodiments less than 0.5%, or less than 0.2%.

Once the intersterification to form the desired structured lipid has elapsed, steps can be carried out to modify the conditions outside the reaction conditions. In some embodiments, modifications include catalyst inactivation, reducing temperature, reducing applied vacuum, ceasing stirring, or any combination of these changes. The person skilled in the art will appreciate carrying out these changes.

In some embodiments, the reaction temperature during the interesterification reaction is in the range of about 85 ° C to about 92 ° C (about 185 ° F to about 197 ° C). In one embodiment, the temperature for the reaction is approximately 88 ° C (191 ° F). In some embodiments, the reaction is carried out under vacuum.

In some embodiments, the reaction time for intersterification is between about 30 minutes and about 2 hours. In one embodiment, the reaction time is approximately 30, 45, or 55 minutes. In one embodiment, the reaction time is approximately 45 minutes. This reaction time can be controlled, for example, by programmed neutralization of the catalyst. The neutralization of a catalyst such as sodium methoxide can be carried out by any method known to the person skilled in the art. In one embodiment, neutralization of sodium methoxide is carried out with about 0.5 to 0.7 percent by weight of citric acid solution at about 50% strength or about 0.59 percent by weight of solution of Citric acid at approximately 50% strength. The duration of the neutralization phase, in one embodiment, is approximately 20 minutes, although longer or shorter times may be used depending on the particular reactants and catalyst used.

Intersterified structured lipid can be treated to remove any residual soap and / or remove all colored bodies, if necessary. This includes filter media and sources of silica such as TRISYL® S-615 (brand, available from W.R. Grace & Co.) used for refining vegetable oil. The color removal can be with a bleaching clay or the like. In some embodiments, the structured lipid is subjected to deodorization using approaches generally known in the art.

In some embodiments, deodorization is carried out by keeping the reaction product at a temperature of about 214 ° C-226 ° C (417.2 ° F-438.8 ° F) under vacuum of about 0.114-0.870 mbar for about 3-5 or about 4 hours.

In some embodiments, the intersterified structured lipid can be combined with one or more phytosterol esters to form a composition that can be used directly as an edible oil product, or also combined with other components to form the desired final product, as will generally be appreciated by the skilled in the art. For example, this may include combining the composition with one or more edible oils and other food components in recipes for consumable foods and the like.

In some embodiments, compositions comprising structured lipid at levels between about 88 and about 98 percent by weight based on the total weight of the product are provided herein; in some embodiments, within the range between about 90 and about 96 percent by weight; and in some embodiments, between about 92 and about 94 percent by weight. The component

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Phytosterol ester can be included in levels between about 2 and about 12 percent by weight; in some embodiments, between about 4 and about 10 percent by weight; and in some embodiments, between about 6 and about 8 percent by weight, all based on the total weight of the composition. One or more additional edible oils may also be used.

Exemplary phytosterol ester compositions can be found in US Pat. Nos. 6,117,475, 6,139,897, 6,277,431, U.S. application requests Nos. 2002/0031595, and 2002/0045000, international publications Nos. WO 01/13733, WO 01/32029 and WO 01/91587. Specific details regarding phytosterol esters and microparticles of phytosterol esters are found in US Pat. No. 6,087,353 and U.S. application application. No. 2002/0048606.

Phytosterol components that can be used in the compositions provided herein include phytosterols and / or phytostanols or derivatives of these types of compounds. It is known that the presence of the sterol component is useful for lowering serum cholesterol and serum triglyceride levels, as well as improving the effectiveness of the total diet. Without being subject to any particular theory, this can be explained by similarity between their respective chemical structures. Through this explanation, phytosterol displaces cholesterol from the micellar phase, thereby reducing cholesterol absorption and / or competing with the sites of the receptor and / or vehicle in the cholesterol absorption process.

Examples of compounds that fall within the meaning of phytosterol include sitosterol, campesterol, stigmasterol, brasicasterol, demosterol, calinosterol, poriferasterol, coioanaterol, and natural or synthesized forms or derivatives, including isomers. Also included are compounds identified with the term phytostanol, including saturated or hydrogenated phytosterols and all natural or synthesized forms and derivatives, including isomers. It will be appreciated that these components can be modified, such as adding side chains, and also falling within the scope of the term phytosterol.

Phytosterols are typically obtained from natural sources, more typically from the processing of plant oils. Sources include corn oil, wheat germ oil, soy extract, rice extract, rice bran, rapeseed oil and sesame oil, walnut oil, other nut oils, peanut oil, and all Vegetable sources oil. Other sources may include resin oils or soaps such as those that are by-products of the forestry industry, which are called wood sterols.

Phytosterol esters are available from public sources, including Forbes Medi-Tech, Inc. An example is the phytosterol product sold under the name REDUCOL®, a registered trademark of Forbes Medi-Tech, Inc. The compositions are sold under this brand. as cholesterol lowering agents. One of these typical compositions is composed of sterols of plants and stanols that have 14.5% of campesterol, 2.4% of field-ethanol, 50.9% of beta-sitosterol, and 18.9% of sitostanol. The REDUCOL® product is a fine crystalline waxy powder. Its characteristic particle size is such that more than 80% of the particles pass through a 0.8 mm sieve and more than 98% of the particles pass through a 2.0 mm sieve. PHYTROL® phytosterol compositions comprise 38 to 79 percent by weight of sitosterol, based on the total weight of the anhydrous composition, 4 to 25 percent by weight of campesterol, 6 to 18 percent by weight of sitoestanol, and 0 to 14 percent by weight of ethanol field. At least 97 percent by weight of the components are in the form of a sterol ester, and no more than 3 percent by weight are free sterols. An exemplary sterol ester from this point of view is a phyto-S-sterol-10 ester. This has a softening point between 15 ° C and 30 ° C and is substantially insoluble in water at 25 ° C. Such a sterol ester is liquid above 40 ° C.

In some embodiments, the amount of stanol structures included in the phytosterol component is minimal, in some embodiments, not greater than about 20, 15, 10 or 5 percent by weight, based on the total weight of the phytosterol ester component.

Uses of the compositions

The compositions provided herein can be formulated in food products to provide stabilized SDA, and, in which the phytosterol esters are used, to provide adequate levels of phytosterols supplied in the body in order to reduce total cholesterol adsorption. In addition, the MCT structure promotes the metabolism of the oil through the liver system rather than through the lymphatic system, leading to the reduction of fatty tissue deposition for these oleic products when compared to products that incorporate similar amounts of other oils. The compositions are also intended to increase the energy expenditure and oxidation components of the substrate. In addition, SDA is believed to provide unique health benefits. SDA stabilizes when it is interesterified as described above, so that such food products will have greater stability than those that use Echium oil or a physical mixture of highly oleic rapeseed oil, MCT, and Echium oil.

The structured lipid compositions described herein provide excellent compositions for edible oil products that have good clarity, physical properties for such uses, and low levels of trans isomer. The compositions described in this text provide a healthy oil that offer a function such as salad oil, frying and baking while providing health benefits directly associated with the presence of SDA. In some embodiment, structured lipids comprising SDA provided in this text are used in baked goods, dairy products, spreadable foods, margarines, sports products, nutritional bars and infant formulas, food, aquaculture, neutraceutical and medicinal products.

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5 Administration of the structured lipid-based oil composition, which contains phytosterol ester provided herein, can be prepared at advantageous levels when included in a monitored diet. In some embodiment, the administration dose is at least about 0.4 grams of the oil composition per kilogram of body weight per day. In one embodiment, the administration range is between about 0.8 and about 1 gram of this oil per kilogram of body weight per day. In a

10 exemplary monitored diet, 40% of the total energy (approximate in calories) in the diet originates from fat, 45% of the energy from carbohydrates, and 15% of the energy from protein sources. From the source of fat, 70% may be provided by the structured lipid composition.

The following examples present some exemplary embodiments and are intended as a means of illustration and not of limitation. In each of the examples in this text, the percentages indicate the percentage by weight of the total

15 of the mixture, unless otherwise indicated.

Examples

Examples 1-6

In each of examples 1-6, an intersterification charge of highly oleic rapeseed oil, medium chain triglycerides and Echium oil is placed in an intersterification reaction chamber with 0.125% in 20 weight of sodium methoxide 95 % powder, in the proportions indicated in Table 1 below. The chamber was maintained at a temperature of 85 ° C-92 ° C (185 ° F-197 ° C) with a target temperature of 88 ° C (191 ° F). The reaction was carried out in vacuo (approximately 4-75 mmHg, or approximately 18-22 mmHg) for approximately 45 minutes. Then the reaction mixture was neutralized with 0.59% by weight of the total 50% citric acid reaction mixture; neutralization continued for approximately 20 minutes. Then the charge 25 of the neutralization reaction was treated with 0.5 weight percent Trisyl S-615 and a filter medium 0.5 at 90 ° C 94 ° C (194 ° F-201 ° F), mixing for approximately 10 minutes to remove the soaps. After the removal of soaps, the reaction mixture was treated with 0.5% bleaching clays and 0.5% filter medium, if necessary, to remove colored bodies. The reaction mixture was then subjected to a deodorization step maintaining it at a temperature of 214 ° C-226 ° C (417.2 ° F-438.8 ° F) under vacuum at approximately 0.114-0.870 mbar

30 for about 4 hours. Deodorization temperature was lower than typical for such reaction products, due to the volatility of SDA.

Table 1

Example #

Echium oil (g) MCT (g) Rapeseed (g)

one

128.81 150.61 150.61

2

1050 1225 1225

3

600 700 700

4

870 1015 1015

5

660 770 770

6

495 557.5 577.5

Example 7: Stability studies

In this experiment, the stability of the compositions prepared as described in Examples 1-6 above was studied and compared with i) Echium oil, and ii) a physical mixture of highly oleic rapeseed oil, MCT, and Echium oil, when analyzing free fatty acids, anisidine value, peroxide value, oxidative stability, color, and FAME.

Samples for this study were created using high density polyethylene (HDPE) bottles.

40 English) of 907 g (32 oz) containing approximately 907 g (2 pounds) of nitrogen bleached oil. Before dispensing the samples, 200 ppm of tert-butylhydroquinone (TBHQ) was added to the physical mixture and interesterified oils. The three oil categories were placed at three storage temperatures 21ºC (70ºF), 29ºC (85ºF), and 38ºC (100ºF). The data extracted for the samples were as follows: weeks 2, 4, 6, 8, and 10. The samples were extracted from their respective labeled bottles and subjected to analytical analyzes that included free fatty acids, anisidine value, value of peroxide, oxidative stability, color, and fatty acid methyl ester (FAME). FAME was carried out using the fish oil method in order to detect the SDA in the oil (AOCS method # Ce 1i-07).

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Peroxide values are provided for the samples in Table 2.

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As can be seen from the data in Table 2, the physical and intersterified mixtures were comparable with respect to peroxide values throughout the study. At 21ºC (70ºF) the intersterified sample behaved

5 better than pure echium oil and physical mixture. At high (29ºC (85ºF) and 38ºC (100ºF)) the peroxide values of the intersterified samples were greater than the physical mixture towards the end of the study; however, on average the peroxide value was lower in the intersterified samples. Pure echium oil had a significant increase in the value of peroxides throughout the study in all three temperature environments.

As can be seen from the data in Table 3, on average, there were no significant changes in FFA values.

10 (free fatty acids) between physical mixtures versus chemically interesterified throughout the 10-week study. Pure echium oil had higher FFA values than both physically and chemically interesterified mixtures.

As can be seen from the data in Table 4, at 21ºC (70ºF) the samples of physical mixtures showed the lowest decrease of the OSI values (oxidative stability index) and ended up having the OSI values more high when compared to the intersterified sample. Although the samples of physical mixtures had higher OSI values than the intersterified mixture, the optimum storage temperature environment for both mixtures appears at 21 ° C (70 ° F). The data shows that the physical mixtures worked well compared to the intersterified mixture for the OSI study. Both physical and intersterified mixtures were significantly more stable than pure echium oil throughout the three environments.

20 temperature throughout the study.

As can be seen from the data in Table 5, the samples of intersterified mixtures have significantly lower anisidine values when compared to the samples of physical mixtures and pure echium oil.

As can be seen from the data in Table 6, the yellow color increased at a constant rate throughout

5 the study. The yellow color in the intersterified samples began to darken more than the physical ones, which can be attributed to the oil processing. Pure echium oil was darker throughout the study compared to physical and chemically interesterified mixtures.

As can be seen from the data in Table 7, the red color increased at a constant rate throughout the study. The red color in the intersterified samples began to darken more than the physical ones which may

10 attributed to oil processing. The pure echium oil was darker than the physical and chemically interesterified mixtures.

As can be seen in the previous data, it was observed that the SDA present in the chemically and intersterified physical oils did not degrade over the 10 weeks. The percentages of intersterified SDA are slightly lower than for the physical mixture due to a slight excess of baking.

15 Based on the calculations of the SDA content present in echium oil, the theoretical SDA content in the intersterified mixture is 3,798% SDA. The current intersterified values coincide with the theoretical values.

Example 8: panel of sensory experts

In this study, oil samples were tested for changes in aroma notes between physical and intersterified mixtures in environments of varying temperatures using a panel of sensory experts. The

20 temperatures used in the study were 21ºC (70ºF) and 29ºC (85ºF). The data from the sensory study is shown below in Tables 8 and 9. If none of the panel experts observed an aroma, then the value was zero.

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The leguminous aroma was observed to a more intense degree in the physical mixture when compared with the intersterified mixture in environments at 21 ° C (70 ° F). The intersterified mixture in the environment at 29 ° C (85 ° F) had a higher intensity degree compared to the physical mixture.

The aged aroma was observed to a more intense degree in the physical mixture when compared with the intersterified mixture in 21ºC (70ºF) environments. The physical mixture in the environment at 29 ° C (85 ° F) had a higher degree of intensity before in the study when compared to the intersterified mixture.

The intersterified mixture on average had a lower herbaceous score throughout the study compared to the physical mixture.

Fishy aroma was constantly observed in the physical mixture and typically more intense when compared to the intersterified mixture.

In the samples around 21ºC (70ºF), the panel observed more intense rancid aromas in the physical mixture samples when compared with the intersterified mixtures.

Walnut notes observed by the panel were present in chemically intersterified mixtures rather than in physical mixtures.

The fruity notes observed by the panel were present in chemically intersterified mixtures rather than in physical mixtures.

The ground notes observed by the panel were similar in both physical mixtures and chemically interesterified.

The physical mixture had more intense rubber notes than the chemically interesterified mixtures.

The physical mixture had more intense paint notes than chemically interesterified mixtures.

The data shows that intersterified oil is less likely to develop many negative residual odors over time when compared to physically mixed oil especially with regard to fishy, rancid, and paint notes. The panel noted that intersterified samples tended to be very clear and pleasant in contrast to samples of physical mixtures often described as fishy.

or stale Example 9: use of marinades In this study, intersterified oil samples were used to prepare marinades using the following

formula. Duplicate batches were prepared for each marinade with each oil to be tested. Marinated white wine 1 ½ glass of white wine ¼ glass of oil 1 small onion, rolled 1 lemon, cut and squeezed 1 tablespoon of dried tarragon 1 small spoon of black pepper Marinated in lime and chili 1 glass of lime juice 1 ½ jalapeno pepper 4 cloves of garlic 1 large onion, rolled 1 tablespoon of cayenne pepper ½ small spoon of salt ¼ glass of oil

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Approximately 454 g (16 ounces) of chicken breast meat was added, which was cut into strips in the marinade of white wine prepared with intersterified oil and marinated in white wine prepared with extra virgin olive oil. Both chicken and marinade mixes were stored overnight in the refrigerator.

Identical electric pans were heated to 149 ° C (300 ° F). A tablespoon of each oil was added to each pan. The chicken strips were added to the pan and cooked until they were made. The chicken strips were removed and 200 g samples were collected for analysis.

Approximately 340 g (12 ounces) of skirt steak meat was added, which was cut into strips of marinated lime and chili prepared with intersterified oil and marinated in lime and chili prepared with extra virgin olive oil. Both marinade and steak mixes were stored overnight in the refrigerator.

Identical electric pans were heated to 190 ° C (375 ° F). A tablespoon of each oil was added to each pan. Skirt steak strips were added to the pan and cooked until they were made. The steak strips were removed and 200 g samples were collected for analysis.

Intersterified oil samples were compared with the control (soybean oil). No residual odors were observed in the samples of interesterified oil. The interesterified oil samples had a light smoke present that is typical due to the MCTs present in the structured lipid.

Example 10: Baking Use

In this study, the samples of interesterified oil and vegetable oil were used to bake a bun using a Duncan Hines® Yellow Cake Mix and to bake brownies using a Duncan Hines® brownie mix.

The test oil and vegetable oil produced very similar results. No differences in appearance or aroma were observed.

Example 11: use for sauteing

In this study, the intersterified oil sample is used for sautéing. Approximately 1/4 cup of oil was added to an electric pan and heated to approximately 163 ° C (325 ° F). Vegetable oil was used as a control. Approximately 150 g of diced 12.7 mm (½ inch) chicken and 300 g of sauteed vegetables were added to the pan and stirred for approximately 4 minutes.

In Examples 9-11, the amount of stearidonic acid in the oil samples used and the amount of stearidonic acid migrated to food products were analyzed using routine analytical methods. Table 10 below provides the amounts in each food product tested.

Table 10

Delta SDA Migration Chart

Type of sample

% of SDA % migration

Control oil

4.35 100.00

Stir-fry meat & vegetables

4.02 92.00

brownie

2.91 67.00

Yellow bun

2.76 63.00

Muffins

2.35 54.00

Chicken marinade

2.07 47.60

Veal Marinated

1.00 23.00

Example 11: Deodorization temperature study

The interesterified oil was prepared using the proportions described for example 4. The reaction mixture was divided into two batches. A batch was subjected to a deodorization stage keeping it at a temperature of 214 ° C 226 ° C (417.2 ° F-438.8 ° F) under vacuum of approximately 0.495-0.76 mbar for 4 hours. The other batch was subjected to a deodorization stage keeping it at a temperature of 226.2 ° C-232.2 ° C under vacuum of approximately 0.495-0.76 mbar for 4 hours.

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The percentage of SDA before and after the deodorization stages is shown in table 11 below. Table 11

SDA percentage

Temp. 226.2ºC-232.2ºC

Temp. 214ºC-226ºC

Before deodorization

4.42% 4.71%

After deodorization

3.70% 4.37%

Retention ratio

83.71% 92.78%

As can be seen from the data, the lowest deodorization temperature retains higher SDA in the sample.

The embodiments of the claimed subject matter described above are intended to be merely exemplary, and those skilled in the art will recognize, or be able to determine using only routine experiments, several equivalents of specific compounds, materials, and procedures. Such equivalents are considered within the scope of the claimed subject matter and are encompassed in the appended claims.

Claims (12)

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one.

An oleic composition comprising an intersterified structured lipid component and one or more components selected from a phytosterol ester and an additional edible oil; wherein the intersterified structured lipid component is a reaction product of a reactive loading of interesterification, the reactive charge comprising (i) an amount of a medium chain triglyceride having fatty acid chains of C6 to C12 in length, (ii ) an amount of a long-chain domestic oil having chains of C16 fatty acids in length, and (iii) an amount of a source of stearidonic acid, in which the source of stearidonic acid is Echium oil and the amount of Echium oil in the intersterification charge is 20-40 percent by weight based on the total weight of the reactive load.

2.

The composition of claim 1, wherein the amount of Echium oil in the intersterification charge is 30 percent by weight.

3.

The composition of claim 1 or 2, wherein the medium chain triglyceride is selected from the group consisting of caprylic triglyceride, capric triglyceride, and combinations thereof.

Four.

The composition of any one of claims 1-3, wherein the domestic long chain oil is selected from the group consisting of soybean oil, corn oil, cottonseed oil, rapeseed oil, olive oil , peanut oil, safflower oil, sunflower oil, cereal plant oil, and combinations thereof.

5.

The composition of any one of claims 1-4, wherein the amount of medium chain triglyceride is 30 to 40 percent by weight of the intersterification charge.

6.

The composition of any one of claims 1-5, wherein the amount of domestic oil is 30 to 40 percent by weight of the intersterification charge.

7.

The composition of any one of claims 1-6, wherein the amount of medium chain triglyceride is 35 percent by weight and the amount of domestic oil is 35 percent by weight of the intersterification charge.

8.

A method for preparing an intersterified structured lipid, comprising: providing a reactive charge comprising an amount of medium chain triglycerides having carbon chain lengths between C6 and C12, an amount of household oil having carbon chain lengths between C16 and C22, and an amount of a source of stearidonic acid; and intersterify the reactive load to form an intersterified structured lipid,

wherein the source of stearidonic acid is Echium oil and the amount of Echium oil in the intersterification charge is 20-40 percent by weight based on the total weight of the reactive charge.

9.

The method of claim 8, wherein the interesterification is catalyzed by a chemical catalyst.

10.

The method of claim 9, wherein the catalyst comprises sodium methoxide.

eleven.

The method of any one of claims 8-10, further comprising a deodorization step.

12.

The method of claim 11, wherein the deodorization is carried out at 214 ° C to 226 ° C.

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